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The title compound, C5H18N2O, reveals a cistrans stereochemistry for this rare example of the 5H-indolizino[1,2-b]indole ring system.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053669/tk2112sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053669/tk2112Isup2.hkl
Contains datablock I

CCDC reference: 634065

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.056
  • wR factor = 0.239
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 30 Perc.
Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

5-Methyl-5 bβ,6,7,8,9,11aα-hexahydro-5H-indolizino[1,2-b]indol-11(5aαH)-one top
Crystal data top
C15H18N2OF(000) = 520
Mr = 242.31Dx = 1.270 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 20 reflections
a = 8.008 (2) Åθ = 6.2–9.3°
b = 17.862 (4) ŵ = 0.08 mm1
c = 8.888 (3) ÅT = 296 K
β = 94.53 (3)°Prism, colorless
V = 1267.4 (6) Å30.50 × 0.40 × 0.30 mm
Z = 4
Data collection top
Rigaku AFC-6S
diffractometer
877 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
ω/2θ scansh = 010
Absorption correction: ψ scan
(North et al., 1968)
k = 023
Tmin = 0.961, Tmax = 0.976l = 1111
2912 measured reflections3 standard reflections every 150 reflections
2912 independent reflections intensity decay: 0.6%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.239 w = 1/[σ2(Fo2) + (0.1076P)2 + 0.3217P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2912 reflectionsΔρmax = 0.30 e Å3
165 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.007 (2)
Special details top

Experimental. 1H NMR (300 MHz, CDCl3): δ 7.38–7.41 (d, J = 7.3 Hz, 1H), 7.10–7.16 (tt, J = 0.9, 8.0 Hz, 1H), 6.68–6.73 (td, J = 1.0, 7.3 Hz, 1H), 6.40–6.42 (d, J = 7.7 Hz, 1H), 4.12–4.17 (dd, J = 4.5, 13.2 Hz, 1H), 4.06–4.10 (d, J = 9.4 Hz, 1H), 3.83–3.86 (dd, J = 2.1, 9.4 Hz, 1H), 3.46–3.52 (dt, J = 2.5, 11.8 Hz, 1H), 2.86 (s, 3H), 2.59–2.69 (td, J = 3.4, 12.8 Hz, 1H), 1.93–1.97 (m, 2H), 1.21–1.70 (m, 4H); 13 C (75 MHz, CDCl3): δ 170.6, 151.0, 128.6, 125.1, 124.9, 118.0, 106.1, 69.2, 62.9, 48.9, 40.6, 33.4, 26.7, 24.6, 23.9; IR (cm-1, neat): 2922, 2856, 2344, 1678, 1606, 1489, 1439, 1300, 1254. ?

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7501 (4)0.04969 (18)0.0702 (3)0.0630 (10)
N10.7524 (5)0.0160 (2)0.4063 (4)0.0621 (12)
N20.7002 (4)0.0594 (2)0.0532 (4)0.0486 (10)
C10.8670 (6)0.1667 (3)0.1398 (5)0.0572 (13)
H10.96750.14750.10110.072*
H20.90030.19690.22650.072*
C20.7738 (7)0.2133 (3)0.0192 (6)0.0698 (16)
H30.68050.23610.06350.084*
H40.84620.25270.00950.084*
C30.7112 (6)0.1666 (3)0.1165 (5)0.0612 (14)
H50.64460.19620.18820.073*
H60.80570.14780.16740.073*
C40.6085 (6)0.1000 (3)0.0687 (5)0.0591 (13)
H70.58240.06680.15180.079*
H80.50620.11750.03310.079*
C50.7689 (5)0.0088 (3)0.0402 (5)0.0484 (12)
C60.8741 (5)0.0250 (3)0.1855 (5)0.0451 (11)
H90.99030.03190.16560.054*
C70.8130 (5)0.0898 (2)0.2764 (5)0.0426 (11)
C80.8139 (6)0.1655 (3)0.2502 (5)0.0544 (12)
H100.85760.18450.16410.065*
C90.7485 (6)0.2136 (3)0.3542 (6)0.0633 (14)
H110.74590.26500.33710.076*
C100.6882 (6)0.1844 (3)0.4817 (6)0.0661 (15)
H120.64610.21700.55100.079*
C110.6874 (6)0.1084 (3)0.5114 (5)0.0560 (13)
H130.64710.08970.59930.067*
C120.7485 (5)0.0615 (3)0.4059 (5)0.0479 (11)
C130.8540 (6)0.0431 (2)0.2878 (5)0.0496 (12)
H140.96290.06170.33010.059*
C140.7619 (6)0.1019 (2)0.1874 (5)0.0490 (11)
H150.66640.12130.23810.059*
C150.7468 (7)0.0595 (3)0.5423 (5)0.0682 (15)
H160.63230.07040.55910.082*
H170.80700.10540.53210.082*
H180.79730.03150.62620.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.078 (2)0.068 (2)0.0438 (19)0.013 (2)0.0139 (17)0.0094 (18)
N10.099 (3)0.046 (3)0.044 (2)0.006 (2)0.018 (2)0.0018 (19)
N20.044 (2)0.054 (2)0.047 (2)0.0061 (19)0.0001 (17)0.008 (2)
C10.068 (3)0.045 (3)0.059 (3)0.007 (2)0.009 (3)0.003 (2)
C20.096 (4)0.051 (3)0.064 (3)0.000 (3)0.019 (3)0.003 (3)
C30.068 (3)0.059 (3)0.057 (3)0.013 (3)0.011 (3)0.019 (3)
C40.049 (3)0.073 (3)0.055 (3)0.005 (3)0.001 (2)0.012 (3)
C50.046 (3)0.052 (3)0.049 (3)0.007 (2)0.019 (2)0.002 (2)
C60.035 (2)0.055 (3)0.046 (2)0.004 (2)0.0057 (19)0.001 (2)
C70.042 (2)0.036 (3)0.050 (3)0.001 (2)0.000 (2)0.006 (2)
C80.057 (3)0.050 (3)0.056 (3)0.002 (2)0.003 (2)0.000 (3)
C90.068 (3)0.044 (3)0.077 (4)0.003 (3)0.004 (3)0.008 (3)
C100.057 (3)0.074 (4)0.067 (4)0.003 (3)0.004 (3)0.027 (3)
C110.056 (3)0.063 (3)0.050 (3)0.007 (3)0.011 (2)0.012 (3)
C120.046 (3)0.055 (3)0.043 (3)0.003 (2)0.005 (2)0.001 (2)
C130.055 (3)0.047 (3)0.046 (3)0.003 (2)0.004 (2)0.004 (2)
C140.050 (3)0.050 (3)0.048 (3)0.001 (2)0.008 (2)0.001 (2)
C150.090 (4)0.067 (3)0.048 (3)0.014 (3)0.003 (3)0.010 (3)
Geometric parameters (Å, º) top
O1—C51.222 (5)C6—C71.514 (6)
N1—C121.385 (6)C6—C131.534 (6)
N1—C151.440 (6)C6—H90.9690
N1—C131.463 (5)C7—C81.373 (6)
N2—C51.346 (6)C7—C121.393 (6)
N2—C41.454 (6)C8—C91.393 (6)
N2—C141.467 (5)C8—H100.9300
C1—C21.507 (7)C9—C101.369 (7)
C1—C141.511 (6)C9—H110.9300
C1—H10.9625C10—C111.383 (7)
C1—H20.9617C10—H120.9300
C2—C31.519 (7)C11—C121.375 (6)
C2—H30.9626C11—H130.9300
C2—H40.9587C13—C141.530 (6)
C3—C41.526 (7)C13—H140.9800
C3—H50.9571C14—H150.9800
C3—H60.9710C15—H160.9600
C4—H70.9572C15—H170.9600
C4—H80.9539C15—H180.9600
C5—C61.513 (6)
C12—N1—C15122.6 (4)C13—C6—H9110.9
C12—N1—C13110.0 (4)C8—C7—C12120.3 (4)
C15—N1—C13118.8 (4)C8—C7—C6131.0 (4)
C5—N2—C4125.0 (4)C12—C7—C6108.7 (4)
C5—N2—C14115.1 (4)C7—C8—C9119.2 (5)
C4—N2—C14117.7 (4)C7—C8—H10120.4
C2—C1—C14111.5 (4)C9—C8—H10120.4
C2—C1—H1108.9C10—C9—C8119.3 (5)
C14—C1—H1109.1C10—C9—H11120.3
C2—C1—H2110.5C8—C9—H11120.3
C14—C1—H2109.3C9—C10—C11122.6 (5)
H1—C1—H2107.5C9—C10—H12118.7
C1—C2—C3112.0 (4)C11—C10—H12118.7
C1—C2—H3107.5C12—C11—C10117.4 (5)
C3—C2—H3109.8C12—C11—H13121.3
C1—C2—H4108.6C10—C11—H13121.3
C3—C2—H4111.0C11—C12—N1128.1 (4)
H3—C2—H4107.7C11—C12—C7121.2 (5)
C2—C3—C4111.0 (4)N1—C12—C7110.7 (4)
C2—C3—H5111.0N1—C13—C14112.1 (4)
C4—C3—H5109.3N1—C13—C6104.7 (3)
C2—C3—H6109.8C14—C13—C6105.5 (3)
C4—C3—H6108.4N1—C13—H14111.4
H5—C3—H6107.1C14—C13—H14111.4
N2—C4—C3110.2 (4)C6—C13—H14111.4
N2—C4—H7109.4N2—C14—C1109.1 (3)
C3—C4—H7111.0N2—C14—C13103.5 (3)
N2—C4—H8108.2C1—C14—C13115.8 (4)
C3—C4—H8109.5N2—C14—H15109.4
H7—C4—H8108.5C1—C14—H15109.4
O1—C5—N2125.7 (5)C13—C14—H15109.4
O1—C5—C6126.6 (4)N1—C15—H16109.5
N2—C5—C6107.7 (4)N1—C15—H17109.5
C5—C6—C7114.8 (3)H16—C15—H17109.5
C5—C6—C13106.1 (4)N1—C15—H18109.5
C7—C6—C13103.7 (3)H16—C15—H18109.5
C5—C6—H9110.3H17—C15—H18109.5
C7—C6—H9110.8
 

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